US4634708AExpiredUtility
Indolophenanthridines useful as dopaminergic and analgesic agents
Est. expiryJan 25, 2004(expired)· nominal 20-yr term from priority
A61P 9/00A61P 37/04A61P 9/12A61P 25/00A61P 25/04A61P 13/02A61P 15/00C07D 457/14C07D 209/90
55
PatentIndex Score
11
Cited by
4
References
17
Claims
Abstract
4,6,6a,7,8,12b-hexahydro-indolo[4,3-ab]phenanthridines are useful as dopaminergic and analgesic agents.
Claims
exact text as granted — not AI-modifiedWhat we claim is:
1. A compound of formula I ##STR16## wherein R 1 and R 3 independently are hydrogen, (C 1-4 )alkyl, (C 3-5 )alkenyl wherein the double bond is not adjacent to the nitrogen atom, (C 3-6 )cycloalkyl(C 1-3 )alkyl, phenyl(C 1-3 )alkyl optionally substituted in the phenyl ring by (C 1-4 )alkyl, (C 1-4 )alkoxy, hydroxy or halogen, or 2- or 3-furyl(C 1-3 )alkyl, R 2 is hydrogen, chlorine, bromine or methyl, X 1 and X 2 independently are hydrogen, (C 1-4 )alkyl, (C 1-4 )alkoxy, hydroxy, halogen or trifluoromethyl, in free base or acid addition salt form.
2. A compound of claim 1 wherein R 1 and R 3 independently are hydrogen, (C 1-4 )alkyl, (C 3-5 )alkenyl wherein the double bond is not adjacent to the nitrogen atom, (C 3-6 )cycloalkyy (C 1-3 )alkyl, phenyl(C 1-3 )alkyl optionally monosubstituted by methyl, methoxy, hydroxy or halogen, or 2- or 3-furyl(C 1-3 )alkyl, R 2 is hydrogen, chlorine, bromine or methyl, X 1 and X 2 independently are hydrogen, (C 1-4 )alkyl, (C 1-4 )alkoxy, hydroxy, halogen or trifluormethyl.
3. A compound of claim 1 wherein R 1 is hydrogen or (C 1-4 )alkyl, R 2 is hydrogen, chlorine, bromine or methyl, R 3 is hydrogen, (C 1-4 )alkyl, benzyl optionally monosubstituted by (C 1-4 )alkoxy, or 2-furylmethyl, X 1 is in position 10, 11 or 12 and is hydrogen, (C 1-4 )alkyl, (C 1-4 )alkoxy, hydroxy, halogen or trifluoromethyl and X 2 is hydrogen.
4. A compound of claim 1 wherein R 1 , R 2 , X 1 and X 2 are hydrogen and R 3 is methyl, in form of the (-)-isomer.
5. A pharmaceutical composition useful in the treatment of Parkinson's disease, conjective cardiac insufficiency, hypertension, renal failure with reduced urine excretion or pain comprising a therapeutically effective amount of a compound according to claim 1 in pharmaceutically acceptable form, in association with a pharmaceutical carrier or diluent.
6. A method of treating a subject suffering from Parkinson's disease, congestive cardiac insufficiency, hypertension, renal failure with reduced urine excretion or pain, which comprises administering a therapeutically effective amount of a compound of claim 1 in pharmaceutically acceptable form.
7. The compound of claim 1, which is trans-4,6,6a,7,8,12b-hexahydro-7-methyl-indolo[4,3-ab] phenanthridine.
8. A compound of claim 1 in which R 2 is hydrogen and R 1 , X 1 , X 2 , and R 3 are respectively: ______________________________________
(a) H H H CH.sub.2CH.sub.3
(b) H H H CH.sub.2CH.sub.2CH.sub.3
(c) CH.sub.3 H H CH.sub.3
(d) H H H CH.sub.2CHCH.sub.2
(e) H H H
##STR17##
(f) H H H
##STR18##
______________________________________
9. A compound of claim 1 in which R 2 is hydrogen and R 1 , X 1 , X 2 and R 3 are respectively: ______________________________________
(g) H 11-OCH.sub.3
H --CH.sub.3
(h) H 11-OH H --CH.sub.3
(i) H 10-OCH.sub.3
H --CH.sub.3
(j) H 10-OH H --CH.sub.3
(k) H 10-CH.sub.3
H --CH.sub.3
(l) H 11-CH.sub.3
H --CH.sub.3
(m) H 10-CF.sub.3
H --CH.sub.3
(n) H 10-CH.sub.3
12-CH.sub.3
--CH.sub.3
(o) H 11-Cl H --CH.sub.3
(p) H 12-OH H --CH.sub.3
______________________________________
10. The compound of claim 1 which is (+)-trans- 4,6,6a,7,8,12b-hexahydro-7-methyl-indolo[4,3-ab]phenanthridine.
11. The compound of claim 1 which is trans-4,6,6a,7,8,12b-hexahydroindolo[4,3-ab]-phenanthridine.
12. The compound of claim 1 in which R 1 is hydrogen R 2 , X 1 , X 2 and R 3 are H,11-OCH 3 , H, and H in racemate form.
13. The compound of claim 1 in which R 1 is hydrogen and R 2 , X 1 , X 2 and R 3 are H, H, H, and H in (-) isomer form.
14. The compound of claim 1 which is trans-4,6,6a,7,8,12b-hexahydro-4,7-dimethyl-indolo[4,3-ab]phenanthridine.
15. The compound of claim 1 in which trans-5-bromo-4,6,6a,7,8,12b-hexahydro-7-methyl-indolo[4,3-ab]phenanthridine.
16. The compound of claim 1 in racemate form in which R 1 , R 2 , R 3 , X 1 and X 2 are respectively: ______________________________________
(a) H Cl --CH.sub.3
H H
(b) H --CH.sub.3
--CH.sub.3
H H
______________________________________
17. The compound of claim 1 in (-) isomer form in which R 1 , R 2 , R 3 , X 1 and X 2 are respectively: ______________________________________
(c) H Br --CH.sub.3
H H
(d) H --CH.sub.3
--CH.sub.3
H H
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